ROLAPITANT

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National Institutes of Health Divider Arrow

NCATS

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C25H26F6N2O2
Molecular Weight	500.4766
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of ROLAPITANT

Structure Search

SMILES

C[C@@H](OC[C@]1(CC[C@]2(CCC(=O)N2)CN1)C3=CC=CC=C3)C4=CC(=CC(=C4)C(F)(F)F)C(F)(F)F

InChI

InChIKey=FIVSJYGQAIEMOC-ZGNKEGEESA-N

InChI=1S/C25H26F6N2O2/c1-16(17-11-19(24(26,27)28)13-20(12-17)25(29,30)31)35-15-23(18-5-3-2-4-6-18)10-9-22(14-32-23)8-7-21(34)33-22/h2-6,11-13,16,32H,7-10,14-15H2,1H3,(H,33,34)/t16-,22-,23-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C25H26F6N2O2
Molecular Weight	500.4766
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:34:23 UTC 2023` Edited by `admin` on `Fri Dec 15 15:34:23 UTC 2023`
Record UNII	NLE429IZUC
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ROLAPITANT

Official Name

English

(5S,8S)-8-{[(1R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethoxy]methyl}-8-phenyl-1,7-diazaspiro[4.5]decan-2-one

Systematic Name

English

ROLAPITANT [USAN]

Common Name

English

ROLAPITANT [MI]

Common Name

English

Rolapitant [WHO-DD]

Common Name

English

1,7-DIAZASPIRO(4.5)DECAN-2-ONE, 8-(((1R)-1-(3,5-BIS(TRIFLUOROMETHYL)PHENYL)ETHOXY)METHYL)-8-PHENYL-, (5S,8S)-

Systematic Name

English

rolapitant [INN]

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000175786

Created by admin on Fri Dec 15 15:34:23 UTC 2023 , Edited by admin on Fri Dec 15 15:34:23 UTC 2023

WHO-ATC

A04AD14

Created by admin on Fri Dec 15 15:34:23 UTC 2023 , Edited by admin on Fri Dec 15 15:34:23 UTC 2023

NCI_THESAURUS

C267

Created by admin on Fri Dec 15 15:34:23 UTC 2023 , Edited by admin on Fri Dec 15 15:34:23 UTC 2023

Code System Code Type Description

NDF-RT

N0000182137

Created by admin on Fri Dec 15 15:34:23 UTC 2023 , Edited by admin on Fri Dec 15 15:34:23 UTC 2023

PRIMARY

Cytochrome P450 2D6 Inhibitors [MoA]

MERCK INDEX

m11844

Created by admin on Fri Dec 15 15:34:23 UTC 2023 , Edited by admin on Fri Dec 15 15:34:23 UTC 2023

PRIMARY

NCI_THESAURUS

C97952

Created by admin on Fri Dec 15 15:34:23 UTC 2023 , Edited by admin on Fri Dec 15 15:34:23 UTC 2023

PRIMARY

ChEMBL

CHEMBL3707331

Created by admin on Fri Dec 15 15:34:23 UTC 2023 , Edited by admin on Fri Dec 15 15:34:23 UTC 2023

PRIMARY

EPA CompTox

DTXSID90203740

Created by admin on Fri Dec 15 15:34:23 UTC 2023 , Edited by admin on Fri Dec 15 15:34:23 UTC 2023

PRIMARY

DRUG BANK

DB09291

Created by admin on Fri Dec 15 15:34:23 UTC 2023 , Edited by admin on Fri Dec 15 15:34:23 UTC 2023

PRIMARY

FDA UNII

NLE429IZUC

Created by admin on Fri Dec 15 15:34:23 UTC 2023 , Edited by admin on Fri Dec 15 15:34:23 UTC 2023

PRIMARY

DAILYMED

NLE429IZUC

Created by admin on Fri Dec 15 15:34:23 UTC 2023 , Edited by admin on Fri Dec 15 15:34:23 UTC 2023

PRIMARY

INN

8882

Created by admin on Fri Dec 15 15:34:23 UTC 2023 , Edited by admin on Fri Dec 15 15:34:23 UTC 2023

PRIMARY

PUBCHEM

10311306

Created by admin on Fri Dec 15 15:34:23 UTC 2023 , Edited by admin on Fri Dec 15 15:34:23 UTC 2023

PRIMARY

DRUG CENTRAL

5027

Created by admin on Fri Dec 15 15:34:23 UTC 2023 , Edited by admin on Fri Dec 15 15:34:23 UTC 2023

PRIMARY

RXCUI

1665496

Created by admin on Fri Dec 15 15:34:23 UTC 2023 , Edited by admin on Fri Dec 15 15:34:23 UTC 2023

PRIMARY

RxNorm

SMS_ID

100000144489

Created by admin on Fri Dec 15 15:34:23 UTC 2023 , Edited by admin on Fri Dec 15 15:34:23 UTC 2023

PRIMARY

EVMPD

SUB121121

Created by admin on Fri Dec 15 15:34:23 UTC 2023 , Edited by admin on Fri Dec 15 15:34:23 UTC 2023

PRIMARY

USAN

CD-170

Created by admin on Fri Dec 15 15:34:23 UTC 2023 , Edited by admin on Fri Dec 15 15:34:23 UTC 2023

PRIMARY

CAS

552292-08-7

Created by admin on Fri Dec 15 15:34:23 UTC 2023 , Edited by admin on Fri Dec 15 15:34:23 UTC 2023

PRIMARY

IUPHAR

5749

Created by admin on Fri Dec 15 15:34:23 UTC 2023 , Edited by admin on Fri Dec 15 15:34:23 UTC 2023

PRIMARY

NDF-RT

N0000190113

Created by admin on Fri Dec 15 15:34:23 UTC 2023 , Edited by admin on Fri Dec 15 15:34:23 UTC 2023

PRIMARY

Breast Cancer Resistance Protein Inhibitors [MoA]

CHEBI

90908

Created by admin on Fri Dec 15 15:34:23 UTC 2023 , Edited by admin on Fri Dec 15 15:34:23 UTC 2023

PRIMARY

WIKIPEDIA

Rolapitant

Created by admin on Fri Dec 15 15:34:23 UTC 2023 , Edited by admin on Fri Dec 15 15:34:23 UTC 2023

PRIMARY

NDF-RT

N0000185503

Created by admin on Fri Dec 15 15:34:23 UTC 2023 , Edited by admin on Fri Dec 15 15:34:23 UTC 2023

PRIMARY

P-Glycoprotein Inhibitors [MoA]

Related Record Type Details


					PUO0521HZV

CYTOCHROME P450 3A4

METABOLIC ENZYME -> SUBSTRATE

Interaction Type:

MAJOR


					6OU487748Q

SUBSTANCE-P RECEPTOR

TARGET -> INHIBITOR

Interaction Type:

ANTAGONIST

Qualification:

Ki

Amount:


					NLE429IZUC

EXCRETED UNCHANGED->SUBSTANCE

Comments:

The total of 46% of the radioactive dose was recovered in urine and feces.In the pooled feces 37.8% of the dose was recovered. Rolapitant was the most prominent component accounting for 12.7% of the dose

Interaction Type:

MAJOR

Qualification:

FECAL

Amount:


					57O5S1QSAQ

ROLAPITANT HYDROCHLORIDE

SALT/SOLVATE -> PARENT


					J7Z9DBN8J0

ROLAPITANT HYDROCHLORIDE ANHYDROUS

SALT/SOLVATE -> PARENT


					6D53G0FD0Z

PLASMA PROTEIN FRACTION (HUMAN)

BINDER->LIGAND

Interaction Type:

BINDING

Amount:


					22ES734693

MULTIDRUG RESISTANCE PROTEIN 1

TRANSPORTER -> NON-SUBSTRATE


					22ES734693

MULTIDRUG RESISTANCE PROTEIN 1

TRANSPORTER -> INHIBITOR

Comments:

[I]/IC50 value for p-gp inhibition was estimated to be 0.23. Based on [I]/IC50 > 0.1 a potential in-vivo drug interaction via inhibition of p-gp cannot be ruled out.

Interaction Type:

INHIBITOR

Qualification:

IC50

Amount:


					8E4LAA4357

CYTOCHROME P450 2D6

METABOLIC ENZYME -> INHIBITOR

Interaction Type:

COMPETITIVE INHIBITOR

Qualification:

Ki

Amount:

Related Record Type Details


					EFL393CK3S

METABOLITE ACTIVE -> PARENT

Comments:

The metabolite SCH 720881 (M19) which accounted 25% of the increased exposure to total plasma radioactivity was identified as a major circulating metabolite of rolapitant.

Interaction Type:

MAJOR

Qualification:

PLASMA

Amount:

Related Record Type Details


					NLE429IZUC

ACTIVE MOIETY

Name	Property Type	Amount	Referenced Substance	Defining	Parameters	References
Biological Half-life	PHARMACOKINETIC

Volume of Distribution	PHARMACOKINETIC